Jesse Livermore: Profit from the World's Most Famous Speculator

For the past few months, I've been warning you about "Bennie and the Crash," due to the Fed's excessive war on inflation. True to form, Wall Street has struggled this summer, and now that the war is heating up in the Middle East, the bear market may continue.

It's the perfect time to do some summer reading, especially about the story of Jesse Livermore, the "boy plunger" of the early 20th century whose story is told in the classic biography, Reminiscences of a Stock Operator.

Under the pseudonym Larry Livingstone, the first-person account reveals in story after story the thrill of victory and the agony of defeat as a speculator extraordinaire. Livermore made and lost a million-dollar fortune three times, and died tragically of suicide in 1940. He lived through the Panic of 1907, the First World War, the Roaring Twenties, the 1929 Crash and the Great Depression.

Throughout it all, he learned many lessons that we can apply todayFive Timeless Rules of Investing Learned From Jesse Livermore

1. "My greatest discovery was that a man must study general conditions, to size them up so as to be able to anticipate probabilities." What did Livermore mean by "general conditions"? He meant the macroeconomic environment and geopolitics. Are they favorable or not favorable to buying stocks? Today, the Fed is raising rates and squeezing the money supply (the monetary base declined last month for the first time in years; a year ago, it was going up 10%.) The war in the Middle East is heating up. These general conditions are not conducive to a bull market, except for gold!

2. Learn from wise old men who have experience in the markets. In Reminiscences of a Stock Operator , the author talks about "the Old Turkey," a "very wise old codger" who counseled Jesse Livermore on making good investment decisions and avoiding mistakes. How can you do this? The best way is to read histories of the great investors such as Warren Buffett, Peter Lynch, John Templeton and J. Paul Getty.

3. Learn your strengths and weaknesses. "We've all got a weak spot. What's yours?" asks the Old Turkey. A good question that we must all answer. "Study mistakes," he counsels. You don't learn from your successes, only from your mistakes!

4. Always save some of your gains. "I was again living pretty well, but always saving something, to increase the stake that I was to take back to Wall Street." Unfortunately, Livermore made the mistake of not living up to his own advice. He leveraged himself too much, and often went bankrupt. By taking some of your gains and investing the funds in alternative investments, such as real estate, art and collectibles, or gold coins, you protect yourself in case you are wrong.

This reminds me of something that happened to me many years ago. I had made a $2 million profit on a penny stock and my wife sat me down and insisted I pay off the mortgage, which was sizeable. I told her I preferred to reinvest the profits in more penny stocks, but she insisted, and I finally agreed with her and paid off the mortgage. It was the best decision "I" ever made! Had I invested the profits in more penny stocks, I would have lost my shirt, because the penny stocks went into a major bear market soon after.

5. Beware the charismatic financial guru! "It cost me millions to learn that another dangerous enemy to a trader is his susceptibility to the urgings of a magnetic personality when plausibly expressed by a brilliant mind." Oh, how true. I well remember the times I invested in several tax shelters that eventually went bust, because I was thoroughly convinced by a smooth talking salesman who seemed brilliant at the time.

To tell you the truth, I hate it when subscribers to my newsletter come up to me and say, "I've cancelled all my other newsletters except yours. You are my guru!" I tell them they are making a mistake. It's best to get the advice of several respected investment advisors and then make up your own mind.

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